58. Acetoacetanilide

Nomenclature

CAS number: 102-01-2
3-Oxo-N-phenylbutanamide; α-acetylacetanilide; acetoacetic anilide; β-ketobutyranilide.
C10H11NO2; mol wt 177.20.
C 67.78%, H 6.26%, N 7.90%, O 18.06%.

Description and references

Prepd by the reaction of ketene dimer with aniline: Chick, Wilsmore, J. Chem. Soc. 1908, 946; Boese, Ind. Eng. Chem. 32, 16 (1940); Williams, Krynitsky, Org. Synth. coll. vol. III, 10 (1955). By the reaction of aniline with ethyl acetoacetate: Knorr, Ann. 26, 69 (1886); Roos, Ber. 21, 624 (1883); Knorr, Reuter, Ber. 27, 1169 (1894). Enol form (unstable) prepd by pouring an alkaline soln of the keto form in cold, dilute H2SO4.

Chemical structure

Derivative

Ketone Form.

Properties

Leaflets from dilute alcohol, mp 85°. Slightly soluble in water; sol in alcohol, chloroform, ether, hot benzene, hot petr ether, acids, or alkali hydroxide solns. Gives a violet color with ferric chloride.

Use

Manuf of yellow dyes, such as Hansa and benzidine yellows. In rubber compounding. In organic syntheses.